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Acetone

2007 Schools Wikipedia Selection. Related subjects: Chemical compounds

                                                                   Acetone
    Acetone Ball-and-stick model of acetone Space-filling model of acetone
                                                                   General
                                                 Systematic name Propanone
                                                Other names β-ketopropane
                                                          Dimethyl ketone,
                                            Molecular formula CH[3]COCH[3]
                                                            SMILES CC(=O)C
                                                    Molar mass 58.09 g/mol
                                               Appearance Colorless liquid
                                                      CAS number [67-64-1]
                                                                Properties
                                     Density and phase 0.79 g/cm³, liquid
                                              Solubility in water miscible
                                       Melting point −94.9 °C (178.2 K)
                                          Boiling point 56.3 °C (329.4 K)
                                              Viscosity 0.32 c P at 20 °C
                                                                 Structure
                                    Molecular shape trigonal planar at C=O
                                                      Dipole moment 2.91 D
                                                                   Hazards
                                                        MSDS External MSDS
                                           EU classification Flammable (F)
                                                             Irritant (Xi)
                                                                  NFPA 704

   3
   1
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                                              R-phrases R11, R36, R66, R67
                                              S-phrases (S2), S9, S16, S26
                                                     Flash point −20 °C
                                                          Flammable limits
                                         in air (by volume) 2.55% - 12.80%
                                          Autoignition temperature 465 °C
                                                   RTECS number AL31500000
                                                   Supplementary data page
                                     Structure & properties n, ε[r], etc.
                                        Thermodynamic data Phase behaviour
                                                        Solid, liquid, gas
                                             Spectral data UV, IR, NMR, MS
                                                         Related compounds
                                                  Related ketones Butanone
                                                    Related solvents Water
                                                                   Ethanol
                                                               Isopropanol
                                                                   Toluene
                          Except where noted otherwise, data are given for
                     materials in their standard state (at 25°C, 100 kPa)
                                         Infobox disclaimer and references

   The chemical compound acetone (also known as propanone, dimethyl
   ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest
   representative of the ketones. Acetone is a colorless, mobile,
   flammable liquid with melting point of −95.4 °C and boiling point of
   56.53 °C. It has a relative density of 0.819 (at 0 °C). It is readily
   soluble in water, ethanol, ether, etc., and itself serves as an
   important solvent.

   The most familiar household use of acetone is as the active ingredient
   in nail polish remover. Acetone is also used to make plastic, fibers,
   drugs, and other chemicals.

   Before the invention of the cumene process acetone was produced by the
   dry distillation of acetates, for example calcium acetate.

   In addition to being manufactured as a chemical, acetone is also found
   naturally in the environment, including in small amounts in the human
   body.

Uses

   An important industrial use for acetone involves its reaction with
   phenol for the manufacture of bisphenol A. Bisphenol A is an important
   component of many polymers such as polycarbonates, polyurethanes and
   epoxy resins. Acetone is also used extensively for the safe
   transporting and storing of acetylene. Vessels containing a porous
   material are first filled with acetone followed by acetylene, which
   dissolves into the acetone. One liter of acetone can dissolve around
   250 liters of acetylene.

   Acetone is often the primary (or only) component in nail polish
   remover. Acetonitrile, another organic solvent, is sometimes used as
   well. Acetone is also used as a superglue remover. It can be used for
   thinning and cleaning fibreglass resins and epoxies. It is a strong
   solvent for most plastics and synthetic fibres.

   Additionally, acetone is extremely effective when used as a cleaning
   agent when dealing with permanent markers. Also acetone can be used as
   an artistic agent; when rubbed on the back of any laser print or laser
   photocopy it produces a rough ready effect.

   Acetone has been used in the manufacture of cordite. During World War I
   a new process of producing acetone through bacterial fermentation was
   developed by Chaim Weizmann, the first president of Israel, in order to
   help the British war effort.

   Acetone can also dissolve many plastics, including those used in
   consumer-targeted Nalgene bottles. Acetone is also used as a drying
   agent, due to the readiness with which it mixes with water, and its
   volatility.

   In the laboratory, acetone is used as a polar aprotic solvent in a
   variety of organic reactions, such as S[N]2 reactions.

   Another industrial application is to use it as a general purpose
   cleaner in paint and ink manufacturing operations.

Use as an automotive fuel additive

   Some automotive enthusiasts add acetone at around 1 part in 500 to
   their fuel, following claims of improved economy. The practice is
   controversial as acetone may affect fuel system parts, such as rubber
   seals. Reports of vehicles covering 50,000 miles (80,000 km) without
   fault would suggest that the percentage 0.2% acetone to fuel ratio will
   not adversely affect any parts, pipes, seals etc.

Health effects

   Acetone is an irritant and inhalation may lead to hepatotoxic effects
   (causing liver damage). The fumes should be avoided. Always use goggles
   when handling acetone; it can cause permanent eye damage ( corneal
   clouding).

   Small amounts of acetone are metabolically produced in the body, mainly
   from fat. In humans, fasting significantly increases its endogenous
   production (see ketosis). Acetone can be elevated in diabetes.
   Contamination of water, food (e.g. milk), or the air (acetone is
   volatile) can lead to chronic exposure to acetone. A number of acute
   poisoning cases have been described. Relatively speaking, acetone is
   not a very toxic compound; it can, however, damage the mucosa of the
   mouth and can irritate and damage skin. Accidental intake of large
   amounts of acetone may lead to unconsciousness and death.

   The effects of long-term exposure to acetone are known mostly from
   animal studies. Kidney, liver, and nerve damage, increased birth
   defects, and lowered reproduction ability of males (only) occurred in
   animals exposed long-term. It is not known if these same effects would
   be exhibited in humans.

   Interestingly, acetone has been shown to have anticonvulsant effects in
   animal models of epilepsy, in the absence of toxicity, when
   administered in millimolar concentrations. It has been hypothesized
   that the high fat low carbohydrate ketogenic diet used clinically to
   control drug-resistant epilepsy in children works by elevating acetone
   in the brain.
     * Acetone (data page)

Safety

   Due to incompatibilities, it is recommended to keep acetone away from
   bromine, chlorine, nitric acid, sulfuric acid and Trichloromethane.
   Retrieved from " http://en.wikipedia.org/wiki/Acetone"
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   with only minor checks and changes (see www.wikipedia.org for details
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